综述与进展

铱催化烯丙基酯的不对称烯丙基取代反应研究进展

  • 邓颖颍 ,
  • 杨文 ,
  • 杨新 ,
  • 杨定乔
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  • 华南师范大学化学与环境学院 教育部环境理论化学重点实验室 广州 510006

收稿日期: 2017-04-19

  修回日期: 2017-06-21

  网络出版日期: 2017-08-11

基金资助

国家自然科学基金(Nos.21172081,21372090)、广东省自然科学基金重点(No.S2013020013091)和广州市科技计划(No.201510010054)资助项目.

Progress in Iridium-Catalyzed Asymmetric Allylic Substitution Reactions with Allylic Esters

  • Deng Yingying ,
  • Yang Wen ,
  • Yang Xin ,
  • Yang Dingqiao
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  • Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou 510006

Received date: 2017-04-19

  Revised date: 2017-06-21

  Online published: 2017-08-11

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21172081, 21372090), the Natural Science Foundation of Guangdong Province (No. S2013020013091) and the Science and Technology Plan Projects of Guangzhou City (No. 201510010054).

摘要

铱催化不对称烯丙基取代反应是一种合成手性化合物的重要方法之一.综述了近年来铱催化烯丙基酯衍生物不对称烯丙基取代反应的研究进展,重点讨论了铱催化剂和烯丙基酯衍生物底物的结构、亲核试剂类型、溶剂及添加剂等因素对烯丙基不对称取代反应的影响,并对可能的反应机理进行了讨论.

本文引用格式

邓颖颍 , 杨文 , 杨新 , 杨定乔 . 铱催化烯丙基酯的不对称烯丙基取代反应研究进展[J]. 有机化学, 2017 , 37(12) : 3039 -3059 . DOI: 10.6023/cjoc201704034

Abstract

Iridium-catalyzed asymmetric allylic substitution reaction is one of the most important methods for the synthesis of chiral compounds. The recent research progress in iridium-catalyzed asymmetric allylic substitution reactions of allylic ester and its derivatives is reviewed with focus on the influences of the iridium catalysts, the substrate structures of allylic ester and its derivatives, the type of nucleophiles, the effects of solvents and additives on asymmetric substitution reaction. Moreover, the possible mechanisms are also discussed in this review.

参考文献

[1] (a) Liu, Z.-Q.; Du, H.-F. Org. Lett. 2010, 12, 3054.
(b) Zhang, P.; Le, H.; Kyne, R. E.; Morken, J. P. J. Am. Chem. Soc. 2011, 133, 9716.
(c) Suetsugu, S.; Nishiguchi, H.; Tsukano, C.; Takemoto, Y. Org. Lett. 2014, 16, 996.
(d) Katcher, M. H.; Norrby, P. O.; Doyle, A. G. Organometallics 2014, 33, 2121.
[2] (a) Hughes, D. L.; Lloyd-Jones, G. C.; Krska, S. W.; Gouriou, L.; Bonnet, V. D.; Jack, K.; Sun, Y.-K.; David, J. M.; Reamer, R. A. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5379.
(b) Litto, R. D.; Benessere, V.; Ruffo, F.; Moberg, C. Eur. J. Org. Chem. 2009, 1352.
[3] Moberg, C. Top Organomet. Chem. 2012, 38, 209.
[4] (a) Jegelka, M.; Plietker, B. Org. Lett. 2009, 11, 3462.
(b) Jegelka, M.; Plietker, B. Chem. Eur. J. 2011, 17, 10417.
[5] (a) Trost, B. M.; Rao, M.; Dieskau, A. P. J. Am. Chem. Soc. 2013, 135, 18697.
(b) Kawatsura, M.; Uchida, K.; Terasaki, S.; Tsuji, H.; Minakawa, M.; Itoh, T. Org. Lett. 2014, 16, 1470.
[6] Tan, Z.-Z.; Wan, X.-L.; Zang, Z.-H.; Qian, Q.; Deng, W.; Gong, H.-G. Chem. Commun. 2014, 50, 3827.
[7] (a) Vrieze, D. C.; Hoge, G. S.; Hoerter, P. Z.; Van Haitsma, J. T.; Samas, B. M. Org. Lett. 2009, 11, 3140.
(b) Arnold, J. S.; Nguyen, H. M. J. Am. Chem. Soc. 2012, 134, 8380.
[8] (a) Yang, S.-C.; Feng, W.-H.; Gan, K.-H. Tetrahedron 2006, 62, 3752.
(b) Zhang, M.; Watanabe, K. J.; Tsukamoto, M.; Shibuya, R.; Morimoto, H.; Ohshima, T. Chem.-Eur. J. 2015, 21, 1.
[9] Guduguntla, S.; Hornillos, V.; Tessier, R.; Fannanaas-Mastral, M.; Feringa, B. L. Org. Lett. 2016, 18, 252.
[10] Tosatti, P.; Nelson, A.; Marsden, S. P. Org. Biomol. Chem. 2012, 10, 3147.
[11] Zhuo, C.-X.; Zheng, C.; You, S.-L. Acc. Chem. Res. 2014, 47, 2558.
[12] Hethcox, J. C.; Shockley, S. E.; Stoltz, B. M. ACS Catal. 2016, 6, 6207.
[13] Takeuchi, R.; Kashio, M. Angew. Chem., Int. Ed. 1997, 36, 263.
[14] Janssen, J. P.; Helmchen, G. Tetrahedron Lett. 1997, 38, 8025.
[15] Butt, N. A.; Zhang, W.-B. Chem. Soc. Rev. 2015, 44, 7929.
[16] Helmchen, G.; Dahnz, A.; Dubon, P.; Schelwies, M.; Weihofen, R. Chem. Commun. 2007, 675.
[17] Wu, Y.-J.; Long, Y.-H.; Yang, D.-Q. Chin. J. Org. Chem. 2009, 29, 1522(in Chinese). (吴钰娟, 龙玉华, 杨定乔, 有机化学, 2010, 29, 1522.)
[18] Giacomina, F.; Riat, D.; Alexakis, A. Org. Lett. 2010, 12, 1156.
[19] Stanley, L. M.; Bai, C.; Ueda, M.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 8918.
[20] Zhao, Z.-L.; Gu, Q.; Wu, X.-Y.; You, S.-L. Chin. Chem. Lett. 2016, 27, 619.
[21] Bondzic, B. P.; Farwick, A.; Liebich, J.; Eilbracht, P. Org. Biomol. Chem. 2008, 6, 3723.
[22] Liu, W.-B.; Zheng, S.-C.; He, H.; Zhao, X.-M.; Dai, L.-X.; You, S.-L. Chem. Commun. 2009, 6604.
[23] Zhang, H.-B.; Chen, J.-T.; Zhao, X.-M. Org. Biomol. Chem. 2016, 14, 7183.
[24] Liu, W.-B.; Zheng, C.; Zhuo, C.-X.; Dai, L.-X.; You, S.-L. J. Am. Chem. Soc. 2012, 134, 4812.
[25] Xu, Q.-L.; Dai, L.-X.; You, S.-L. Adv. Synth. Catal. 2012, 354, 2275.
[26] Zhan, M.; Li, R.-Z.; Mou, Z.-D.; Cao, C.-G.; Liu, J.; Chen, Y.-W.; Niu, D.-W. ACS Catal. 2016, 6, 3381.
[27] (a) Trost, B. M.; Jiang, C. H. Synthesis 2006, 369.
(b) Behenna, D. C.; Stoltz, B. M. Top Organomet. Chem. 2013, 44, 281.
[28] Chen, W.-Y.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 2068.
[29] Chen, W.-Y.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 377.
[30] Liu, W.-B.; Reeves, C. M.; Virgil, S. C.; Stoltz, B. M. J. Am. Chem. Soc. 2013, 135, 10626.
[31] Liu, W.-B.; Reeves, C. M.; Stoltz, B. M. J. Am. Chem. Soc. 2013, 135, 17298.
[32] Liu, W.-B.; Okamoto, N.; Alexy, E. J.; Hong, A. Y.; Tran, K.; Stoltz, B. M. J. Am. Chem. Soc. 2016, 138, 5234.
[33] Liu, J.; Cao, C.-G.; Sun, H.-B.; Zhang, X.; Niu, D.-W. J. Am. Chem. Soc. 2016, 138, 13103.
[34] (a) Krautwald, S.; Schafroth, M. A.; Sarlah, D.; Carreira, E. M. J. Am. Chem. Soc. 2014, 136, 3020.
(b) Sandmeier, T.; Krautwald, S.; Zipfel, H. F.; Carreira, E. M. Angew. Chem., Int. Ed. 2015, 54, 14363.
[35] (a) Yao, K.; Liu, D.-L.; Yuan, Q.-J.; Imamoto, T.; Liu, Y.-G.; Zhang, W.-B. Org. Lett. 2016, 18, 6296.
(b) Huo, X.-H.; Yang, G.-Q.; Liu, D.-L.; Liu, Y.-G.; Gridnev, I. D.; Zhang, W.-B. Angew. Chem., Int. Ed. 2014, 53, 6776.
[36] Krautwald, S.; Sarlah, D.; Schafroth, M. A.; Carreira, E. M. Science 2013, 340, 1065.
[37] Wei, X.; Liu, D.-L.; An, Q.-J.; Zhang, W.-B. Org. Lett. 2015, 17, 5768.
[38] Liu, W.-B.; He, H.; Dai, L.-X.; You, S.-L. Org. Lett. 2008, 10, 1815.
[39] Zhou, C.-X.; Wu, Q.-F.; Zhou, Q.; Xu, Q.-L.; You, S.-L. J. Am. Chem. Soc. 2013, 135, 8169.
[40] Zhuo, C.-X.; Cheng, Q.; Liu, W.-B.; Zhao, Q.; You, S.-L. Angew. Chem., Int. Ed. 2015, 54, 8475.
[41] Wu, Q.-F.; Liu, W.-B.; Zhuo, C.-X.; Rong, Z.-Q.; Ye, K.-Y.; You, S.-L. Angew. Chem., Int. Ed. 2011, 50, 4455.
[42] Xu, Q.-L.; Dai, L.-X.; You, S.-L. Org. Lett. 2012, 14, 2579.
[43] Cheng, Q.; Wang, Y.; You, S.-L. Angew. Chem., Int. Ed. 2016, 55, 3496.
[44] Chen, W.-Y.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 15249.
[45] Chen, W.-Y.; Chen, M.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 15825.
[46] Chen, M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2014, 53, 8691.
[47] Chen, M.; Hartwig, J. F. J. Am. Chem. Soc. 2015, 137, 13972.
[48] Chen, M.:Hartwig, J. F. Angew. Chem., Int. Ed. 2014, 53, 12172.
[49] Chen, M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2016, 55, 11651.
[50] Jiang, X.-Y.; Chen, W.-Y.; Hartwig, J. F. Angew. Chem., Int. Ed. 2016, 55, 5819.
[51] Alexakis, A.; Hajjaji, S. E.; Polet, D.; Rathgeb, X. Org. Lett. 2007, 9, 3393.
[52] Polet, D.; Rathgeb, X.; Falciola, C. A.; Langlois, J. B.; Hajjaji, S. E.; Alexakis, A. Chem. Eur. J. 2009, 15, 1205.
[53] Hamilton, J. Y.; Sarlah, D.; Carreira, E. M. Angew. Chem., Int. Ed. 2015, 54, 7644.
[54] Liu, X.-J.; You, S.-L. Angew. Chem., Int. Ed. 2017, 56, 4002.
[55] Breitler, S.; Carreira, E. M. J. Am. Chem. Soc. 2015, 137, 5296.
[56] Pouy, M. J.; Leitner, A.; Weix, D. J.; Ueno, S.; Hartwig, J. F. Org. Lett. 2007, 9, 3949.
[57] Pouy, M. J.; Stanley, L. M.; Hartwig, J. F. J. Am. Chem. Soc. 2009, 131, 11312.
[58] Weihofen, R.; Tverskoy, O.; Helmchen, G. Angew. Chem., Int. Ed. 2006, 45, 5546.
[59] Spiess, S.; Berthold, C.; Weihofen, R.; Helmchen, G. Org. Biomol. Chem. 2007, 5, 2357.
[60] Weix, D. J.; Markovic, D.; Ueda, M.; Hartwig, J. F. Org. Lett. 2009, 11, 2944.
[61] Markovic, D.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 11680.
[62] Ye, K.-Y.; Dai, L.-X.; You, S.-L. Org. Biomol. Chem. 2012, 10, 5932.
[63] Ye, K.-Y.; Dai, L.-X.; You, S.-L. Chem. Eur. J. 2014, 20, 3040.
[64] Stanley, L. M.; Hartwig, J. F. J. Am. Chem. Soc. 2009, 131, 8971.
[65] Liu, W.-B.; Zhang, X.; Dai, L.-X.; You, S.-L. Angew. Chem., Int. Ed. 2012, 51, 5183.
[66] Yang, Z.-P.; Wu, Q.-F.; You, S.-L. Angew. Chem., Int. Ed. 2014, 53, 6986.
[67] Zhang, X.; Yang, Z.-P.; Huang, L.; You, S.-L. Angew. Chem., Int. Ed. 2015, 54, 1873
[68] Yang, Z.-P.; Wu, Q.-F.; Shao, W.; You, S.-L. J. Am. Chem. Soc. 2015, 137, 15899.
[69] Zhuo, C.-X.; Zhang, X.; You, S.-L. ACS Catal. 2016, 6, 5307.
[70] Ye, K.-Y.; Cheng, Q.; Zhuo, C.-X.; Dai, L.-X.; You, S.-L. Angew. Chem., Int. Ed. 2016, 55, 8113.
[71] Yang, Z.-P.; Zheng, C.; Huang, L.; Qian, C.; You, S.-L. Angew. Chem., Int. Ed. 2017, 56, 1530.
[72] Miyabe, H.; Yoshida, K.; Reddy, V. K.; Takemoto, Y. J. Org. Chem. 2009, 74, 305.
[73] Gärtner, M.; Jäkel, M.; Achatz, M.; Sonnenschein, C.; Tverskoy, O.; Helmchen, G. Org. Lett. 2011, 13, 2810.
[74] Lee, J.-H.; Lee, S.-G. Chem. Sci. 2013, 4, 2922.
[75] Satyanarayana, G.; Helmchen, G. Eur. J. Org. Chem. 2014, 2242.
[76] Grange, R. L.; Clizbe, E. A.; Counsell, E. J.; Evans, A. P. Chem. Sci. 2015, 6, 777.
[77] Kimura, M.; Uozumi, Y. J. Org. Chem. 2007, 72, 707.
[78] He, H.; Ye, K.-Y.; Wu, Q.-F.; Dai, L.-X.; You, S.-L. Adv. Synth. Catal. 2012, 354, 1084.
[79] Qu, J.-P.; Roβberg, L.; Helmchen, G. J. Am. Chem. Soc. 2014, 136, 1272.
[80] Zhao, D.-P.; Martin, F. M.; Chang, M.-C.; Otten, E.; Feringa, B. L. Chem. Sci. 2014, 5, 4216.
[81] Zheng, S.-C.; Zhang, M.; Zhao. X.-M. Chem. Eur. J. 2014, 20, 1.
[82] Zhang, M.; Zheng, S.-C.; Zhao, X.-M. Chem. Commun. 2014, 50, 4455.
[83] Gärtner, M.; Mader, S.; Seehafer, K.; Helmchen, G. J. Am. Chem. Soc. 2011, 133, 2072.
[84] Xu, Q.-L.; Dai, L.-X.; You, S.-L. Org. Lett. 2010, 12, 800.
[85] Ueda, M.; Hartwing, J. F. Org. Lett. 2010, 12, 92.
[86] Liu, W.; Zhao, X.-M.; Zhang, H.-B.; Zhang, L.; Zhao, M.-Z. Chem. Eur. J. 2014, 20, 16873.
[87] Zheng, S.-C.; Gao, N.; Liu, W.; Liu, D.-G.; Zhao, X.-M.; Cohen, T. Org. Lett. 2010, 12, 4454.
[88] Zheng, S.-C.; Huang, W.-Q.; Gao, N.; Cui, R.-M.; Zhang, M.; Zhao, X.-M. Chem. Commum. 2011, 47, 6969.
[89] Huang, W.-Q.; Zheng, S.-C.; Tang, J.-L.; Zhao, X.-M. Org. Biomol. Chem. 2011, 9, 7897.
[90] Gao, N.; Zhao, X.-M. Eur. J. Org. Chem. 2013, 2708.
[91] Topczewski, J. J.; Tewson, T. J.; Nguyen, H. M. J. Am. Chem. Soc. 2011, 133, 19318.
[92] Zhang, Q.; Stockdale, D. P.; Mixdorf, J. C.; Topczewski, J. J.; Nguyen, H. M. J. Am. Chem. Soc. 2015, 137, 11912.

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